European Journal of Organic Chemistry, volume 2003, issue 10, pages 1918-1922
A Convenient Synthesis of 1-Deoxy-8a-epi-Castanospermine Diastereoisomers (6R,7R,8S,8aS)-6,7,8-Trihydroxyindolizidine and (6R,7R,8R,8aS)-6,7,8-Trihydroxyindolizidine
Publication type: Journal Article
Publication date: 2003-05-05
scimago Q2
SJR: 0.584
CiteScore: 5.4
Impact factor: 2.5
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
An efficient synthesis of (6R,7R,8S,8aS)-6,7,8-trihydroxyindolizidine and (6R,7R,8R,8aS)-6,7,8-trihydroxyindolizidine is described from readily available N-BOC-L-proline, (BOC = tert-butoxycarbonyl) which involves the addition of ethyl lithiopropiolate to the aldehyde derived from N-BOC-L-proline as a key step, then cyclization to construct indolizidine skeletons and asymmetric dihydroxylation. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
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